O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

Base Information

• Chemical Name: O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose
• CAS No.: 121654-06-6
• Molecular Formula: C₄₇H₅₀O₉
• Molecular Weight: 758.909
• Mol file: 121654-06-6.mol

Synonyms:O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

Chemical Property of O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

There total 3 articles about O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

3,4-di-O-benzyl-D-glucal (58871-10-6) + 3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) → O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose (121654-06-6)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; 1.) -78 deg C, 1 h, 2.) -78 deg C -> r.t., 1 h; r.t., 18 h;

DOI:10.1021/ja00199a028

Reference yield: 12.0%

3,4-di-O-benzyl-D-glucal (58871-10-6) + 3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) → 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-glucal (137792-57-5) + O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose (121654-06-6) + (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3S,4R)-3,4-bis-benzyloxy-3,4-dihydro-2H-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol (153482-11-2)

Guidance literature:

With tert-butylchlorodiphenylsilane; zinc(II) chloride; at -78 - 20 ℃;

DOI:10.1002/recl.19931121107

Reference yield:

3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diethyldithiocarbamate (1380516-32-4) + 3,4-di-O-benzyl-D-glucal (58871-10-6) → O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose (121654-06-6)

Guidance literature:

3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diethyldithiocarbamate; With 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; 1,2-dichloro-ethane; at 20 ℃; for 1h; Molecular sieve;

With copper(I) triflate benzene complex; In dichloromethane; 1,2-dichloro-ethane; at -50 ℃; for 0.166667h;

3,4-di-O-benzyl-D-glucal; In dichloromethane; 1,2-dichloro-ethane; at -50 - -30 ℃; for 15.8333h; stereoselective reaction;

DOI:10.1021/ol301349w

upstream raw materials:

3,4-di-O-benzyl-D-glucal

3,4,6-tri-O-benzyl-D-glucal epoxide

3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diethyldithiocarbamate

Downstream raw materials:

O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-O-(2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-O-(3,4-di-O-benzyl-β-D-glucopyranosyl)-(1->6)-1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-arabino-hex-1-enopyranose

(1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2,7-dioxa-bicyclo[4.1.0]heptane

(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3S,4R)-3,4-bis-benzyloxy-3,4-dihydro-2H-pyran-2-ylmethoxy)-dihydro-pyran-3-one